Guess Where Trips offers surprise excursions for adventurous travelers
Bethune Beach is one of the stops in a surprise road trip itinerary from Guess Where Trips. Credit: TNS/Patrick Connolly
Some road trips require meticulous planning, mapping and calculating to find the best roadside attractions, food stops and gas stations along the way. But for spontaneous, adventurous explorers, a travel company provides this puzzling riddle: Guess Where?
Geared to families, friends and all-day dates, the company Guess Where Trips supplies self-guided itineraries that leave road trippers guessing right up until the moment they leave. The Canada-based firm offers surprise excursions in several U.S. states, as well as four Canadian provinces: British Columbia, Ontario, Alberta and Nova Scotia. Options include trips in the New York City area and around Philadelphia.
Headed south this winter? Guess Where Trips offers six surprise excursions in Florida that harken back to an earlier time in the Sunshine State’s history, when car trips and roadside attractions were all the rage.
Some journeys help explorers delve into the past or embark on outdoor adventures, while others present quaint towns and local fare to eat. Near Gainesville, travel the “Old Florida Trail” or head to South Florida for “Treasure Coast Explorer,” “Mysteries of Miami,” “Outback Oasis” and “Adventure in the Glades.”
For an outing that promises “extraordinary destinations with strange stories and history,” order the “Mysterious Gems” itinerary, which is rated 3/5 for both accessibility and pet-friendliness and 2/5 for activity level.
Before getting in the car, open the (optional) gift box to see what’s in store. A folder with a neatly wrapped postcard and envelope awaits, plus a handy canvas tote bag. It’s wise to read the “Before You Go” envelope, which recommends traveling within six months of receiving the package. A section on the company’s website provides timely updates.
Leaving no stone unturned, Guess Where Trips even provides a playlist with modern-day hits and classics from Fleetwood Mac, Tom Petty, Billy Joel and The Beatles.
IF YOU GO
Mailed trip: With a mailed trip, you will receive five sealed envelopes, including four surprise stop envelopes and a “Before You Go” envelope, which will give you just the right amount of details without ruining the surprise stops. On the day of your road trip, your surprise stops will be revealed to you as you open each envelope. Cost: $65 plus tax for the mailed trip.
PDF Trip: These are great for road trippers who don’t want to wait for their package in the mail. The PDF trips are the same road trip as the mailed option, just in a digital format. Once you purchase a PDF trip, you will receive an email with a link to download your trip. Cost: $39 for the PDF. Note: There are no surprise envelopes with the PDF option. All stops are in one digital file, so scrolling through the document will reveal the surprise stops.
For more information, visit guesswheretrips.com.
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